Madison Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Madison vacation rentals

A bedroom with a large bed, a wooden ceiling, and a view of a balcony with outdoor furniture.

1. Romantic Woodside Cabin | Hot Tub & Fire Pit

Romantic Woodside Cabin | Hot Tub & Fire Pit
Madison
9.6 out of 10, Exceptional, (5 reviews)
"This was an incredible stay for my wife and I. The cleanliness, quietness, and coziness was amazing. We will definitely be back for another anniversary stay. The multiple wineries around also help enhance the stay even more. You’re missing out if you don’t book this cabin. "
United States
Matthew
The price is CA $225
CA $272 total
includes taxes & fees
Nov 23 - Nov 24
Romantic Woodside Cabin | Hot Tub & Fire Pit
A house with a white door, grey steps, and two potted yellow flowers at the entrance.

2. The Blue Grape: Dog-Friendly Wine Country Home, King Bed & Private Deck

The Blue Grape: Dog-Friendly Wine Country Home, King Bed & Private Deck
Madison
The price is CA $195
CA $349 total
includes taxes & fees
Nov 17 - Nov 18
The Blue Grape: Dog-Friendly Wine Country Home, King Bed & Private Deck
A stone patio with four Adirondack chairs in yellow, green, red, and blue, overlooking a body of water with an American flag on a flagpole.

3. LemonDrop Lake-Front Cottage

LemonDrop Lake-Front Cottage
Madison-on-the-Lake
10.0 out of 10, Exceptional, (23 reviews)
"Nice stay"
United States
Michael M.
The price is CA $222
CA $356 total
includes taxes & fees
Nov 15 - Nov 16
LemonDrop Lake-Front Cottage
A dining area with a white table and black chairs, large windows with a view of a green landscape, and a small potted plant on the table.

4. Updated Cottage - Great Location Near Lake, Wineries, and SPIRE Institute!

Updated Cottage - Great Location Near Lake, Wineries, and SPIRE Institute!
Madison-on-the-Lake
10.0 out of 10, Exceptional, (5 reviews)
"Good location and a cute space. "
United States
Veronica K.
The price is CA $191
CA $409 total
includes taxes & fees
Nov 17 - Nov 18
Updated Cottage - Great Location Near Lake, Wineries, and SPIRE Institute!
A living room with a leather couch, a fireplace, and a large window offering a view of the ocean.

5. SeaSide Lake-Front Cottage

SeaSide Lake-Front Cottage
Madison-on-the-Lake
10.0 out of 10, Exceptional, (18 reviews)
"The property was gorgeous! We had such a wonderful relaxing time! The unit has everything you could ever need. Thanks!"
United States
Mary G.
The price is CA $236
CA $372 total
includes taxes & fees
Nov 11 - Nov 12
SeaSide Lake-Front Cottage
A large, multi-story house with a stone facade, a spacious driveway, and a well-maintained lawn.

6. 3-bedroom pet friendly home in Madison walking distance to beach & winery

3-bedroom pet friendly home in Madison walking distance to beach & winery
Madison-on-the-Lake
10.0 out of 10, Exceptional, (2 reviews)
"The host was responsive and kind. The house was very well equipped, clean and comfortable! 5 stars!"
United States
Stacy S.
The price is CA $212
CA $346 total
includes taxes & fees
Nov 15 - Nov 16
3-bedroom pet friendly home in Madison walking distance to beach & winery
A modern living room with a wooden wall, a sofa, a coffee table, and a dining area with chairs.

7. Highland House | Wine Country | Private Hot Tub

Highland House | Wine Country | Private Hot Tub
Madison
The price is CA $281
CA $333 total
includes taxes & fees
Nov 11 - Nov 12
Highland House | Wine Country | Private Hot Tub
A modern living room with a sofa, chairs, and a coffee table. Large windows offer a view of trees.

8. Ledge House Vintage Retreat | Hot Tub & Fire Pit

Ledge House Vintage Retreat | Hot Tub & Fire Pit
Madison
The price is CA $356
CA $418 total
includes taxes & fees
Nov 12 - Nov 13
Ledge House Vintage Retreat | Hot Tub & Fire Pit
A modern kitchen with blue cabinets, a stainless steel dishwasher, a gas stove, and a microwave.

9. Dog-Friendly Retreat Near Wineries/Spire/GOTL

Dog-Friendly Retreat Near Wineries/Spire/GOTL
Madison-on-the-Lake
9.6 out of 10, Exceptional, (39 reviews)
"Amazing stay clean and safe ."
United States
TerriAnn M.
The price is CA $272
CA $432 total
includes taxes & fees
Nov 11 - Nov 12
Dog-Friendly Retreat Near Wineries/Spire/GOTL
A modern dining area with a glass table, chairs, and a potted plant.

10. Hot Tub & Fire Table | Madison, Lake Erie

Hot Tub & Fire Table | Madison, Lake Erie
Madison-on-the-Lake
8.8 out of 10, Excellent, (24 reviews)
"We had a wonderful stay here. My grandkids enjoyed the hot tub. I liked the layout of the house and it was very spacious. We were close to the lake, wineries and restaurants.We would definatly come back again."
United States
Kim K.
The price is CA $323
CA $615 total
includes taxes & fees
Nov 15 - Nov 16
Hot Tub & Fire Table | Madison, Lake Erie
A backyard patio with a table and chairs, a grill, and a barbecue smoker.

11. Charming 2-bedroom house in delightful Madison with AC

Charming 2-bedroom house in delightful Madison with AC
Madison-on-the-Lake
8.0 out of 10, Very good, (5 reviews)
"Beautiful, pet friendly , host was easy to communicate with , we would stay again"
United States
Robin T.
The price is CA $381
CA $429 total
includes taxes & fees
Dec 9 - Dec 10
Charming 2-bedroom house in delightful Madison with AC
A living room with a leather sofa, a dining table with chairs, a TV, a fireplace, and large windows overlooking the ocean.

12. Tree-Top Lake-Front Cottage

Tree-Top Lake-Front Cottage
Madison-on-the-Lake
9.6 out of 10, Exceptional, (20 reviews)
"What an amazing little cottage with wonderful lake views! The cottage was clean and communication with the owner was fantastic! We loved our time here!"
United States
Andrea T.
The price is CA $236
CA $371 total
includes taxes & fees
Nov 11 - Nov 12
Tree-Top Lake-Front Cottage
A cozy living room with a leather sofa, a wooden coffee table, and a large window offering a view of the outdoors.

13. Lakeside Chalet | Private Lake | Hot Tub | Views

Lakeside Chalet | Private Lake | Hot Tub | Views
Madison
The price is CA $422
CA $497 total
includes taxes & fees
Nov 23 - Nov 24
Lakeside Chalet | Private Lake | Hot Tub | Views
A bedroom with a bed, a ceiling fan, a TV on a dresser, and two windows with blinds.

14. A great stay, close to Spire, GOTL, & Wineries....King Bed!

A great stay, close to Spire, GOTL, & Wineries....King Bed!
Geneva
10.0 out of 10, Exceptional, (49 reviews)
"Very clean.. spacious, Close to wineries."
United States
frances f.
The price is CA $127
CA $260 total
includes taxes & fees
Nov 22 - Nov 23
A great stay, close to Spire, GOTL, & Wineries....King Bed!
A living room with a brown sofa, a coffee table, a TV, and a ceiling fan.

15. A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!

A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
Geneva
10.0 out of 10, Exceptional, (24 reviews)
"The accommodations were exactly what we were looking for…everything we needed in a comfortable and cozy spot."
United States
Daniel K.
The price is CA $134
CA $263 total
includes taxes & fees
Nov 16 - Nov 17
A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
A modern kitchen with dark cabinets, a white stove, and a granite countertop.

16. Chardonnay Cottage - GOTL Strip - Cozy & Quaint

Chardonnay Cottage - GOTL Strip - Cozy & Quaint
Geneva
9.8 out of 10, Exceptional, (25 reviews)
"This cottage was very clean & cozy! We would definitely rent this again. Very close to the strip. Would highly recommend staying here!"
United States
James
The price is CA $76
CA $279 total
includes taxes & fees
Nov 11 - Nov 12
Chardonnay Cottage - GOTL Strip - Cozy & Quaint
A small house with solar panels, a porch with outdoor furniture, and a wooden deck.

17. Cozy Shed-Teau in Geneva + Firepit

Cozy Shed-Teau in Geneva + Firepit
Geneva
9.6 out of 10, Exceptional, (15 reviews)
"Very nice property"
United States
William M B.
The price is CA $155
CA $181 total
includes taxes & fees
Nov 16 - Nov 17
Cozy Shed-Teau in Geneva + Firepit
A covered outdoor deck with a black wicker sofa, a small table, and a chair.

18. On The Strip • Cozy GOTL Vacation Cottage

On The Strip • Cozy GOTL Vacation Cottage
Geneva
9.4 out of 10, Exceptional, (112 reviews)
"Very pleasant stay"
United States
Daniel M.
The price is CA $119
CA $362 total
includes taxes & fees
Nov 12 - Nov 13
On The Strip • Cozy GOTL Vacation Cottage
A square fire pit table with two metal chairs on a wooden deck.

19. Beautiful cabin situated on wooded land with nice yard clearing and small stream

Beautiful cabin situated on wooded land with nice yard clearing and small stream
Madison
9.8 out of 10, Exceptional, (14 reviews)
"Wonderful stay :) "
United States
Jennifer S.
The price is CA $184
CA $219 total
includes taxes & fees
Nov 13 - Nov 14
Beautiful cabin situated on wooded land with nice yard clearing and small stream
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden countertop.

20. Recently updated apartment in a Triplex close to Spire Wineries and the Lake.

Recently updated apartment in a Triplex close to Spire Wineries and the Lake.
Geneva
9.4 out of 10, Exceptional, (45 reviews)
"Nice place for a weekend. Good price and everything we needed"
United States
Devan M.
The price is CA $134
CA $235 total
includes taxes & fees
Nov 11 - Nov 12
Recently updated apartment in a Triplex close to Spire Wineries and the Lake.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Madison Hotel Reviews

A Holiday Inn Express & Suites hotel with a modern design, featuring a covered entrance and a well-lit facade.
Holiday Inn Express & Suites Madison by IHG

Holiday Inn Express & Suites Madison by IHG

Holiday Inn Express & Suites Madison by IHG
Madison

10/10 Excellent

The hotel was nice and clean, the staff were friendly. Breakfast had more options than we expected.
Canada
Virgino
Reviewed September 11, 2026
Holiday Inn Express & Suites Madison by IHG

Find out more about Madison

Everything you need to know about Madison vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Madison vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Madison vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Madison vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Madison. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Madison vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Madison vacation rentals we have selected for you start as low as CA $126 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Madison rentals

At Expedia, we put the best Madison vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Madison rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Madison vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Madison. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find a vacation rental in Madison?

Yes, you can find vacation rentals in Madison close to Rabbit Run Community Arts Association, or you can go with a secluded option if you want a relaxing stay. Madison is known for its wineries and theaters. Make sure you have time to check out the restaurants while you're in the area.

What's the top vacation rental in Madison?

Charming 2-bedroom house in delightful Madison with AC: Visitors give good reviews to this Madison vacation home rental, which is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You can relax into your vacation with a garden and a selection of books. Some other top choices in Madison are Lakefront Retreat w/ Private Beach. Sleeps 12 and Lake Erie Beachfront Retreat - 8 BR + Private Beach & Hot tub!.

How many vacation rentals will I find in Madison?

With 38 Expedia vacation rentals, you're sure to find just the right place for your Madison stay.

What can I see and do in Madison?

Lake Erie and Hogback Ridge are a couple of scenic spots to enjoy the outdoors, whereas Rabbit Run Community Arts Association is one of the cultural attractions. While here, Laurentia Vineyard & Winery and Grand River Cellars Winery are other places worth a visit.

What are vacation rentals like in Madison?

Vacation rentals are privately owned properties you can stay in for a couple days or more in Madison. Vacation rentals offer extras such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.